Archive of Our Own ^beta

Chapter Text

Dean loved Cassie. The way she walked. The way she dressed. Her smooth feminine voice. The way she got passionate about the injustices of the world and would go off on a tangent about something that Dean didn’t always fully understand, but was happy to listen to anyway. 

Their relationship had its issues as any relationship did. 

For the first few months after they got together, Dean lied to her about his family. He told her his dad traveled a lot for business. That’s why she could never meet him. He told her his brother was across the country attending Stanford and couldn’t come home to visit because he was just too busy with school and his part-time job. He told her that his mother left when he was young, but that he still went to visit her in upstate New York on the big holidays like Thanksgiving and Christmas. This is why Cassie could never see Dean on holidays. This is why Dean could never meet Cassie’s family on holidays as well.

When they had been dating several months and things were going well, Cassie decided it was time for her to visit Dean at home. She had seen the outside a few times, but never really had an opportunity to be invited in. So she texted Dean to make sure he was home, then put on her favorite pair of black lace panties and matching bralette- the ones she knew Dean loved- and she drove on over to Dean’s house. The house he told her he shared with his dad and brother when they were in town.

Cassie didn’t see Dean’s Impala in the driveway, but the garage was closed, so she figured it was parked in there. She hardly thought anything of it to be honest. But when she knocked on the door and a girl who looked to be about 13 or 14 years old answered, Cassie was confused.

“Hi. Uh… is Dean here?” Cassie asked with a polite smile.

The girl gave her an equally confused look as the one she had just received.

“I think you have the wrong house.”

“Oh.” Cassie said softly. “Do you know of anyone named Dean who lives around here? He’s tall, short brown hair, wears a big leather jacket? He also drives a classic car?”

“No.. I don’t know anyone around here like that.”

“Okay. Sorry to bother you.”

The girl promptly closed the door, leaving Cassie with more questions than answers. She walked back to her car, got inside, and pulled out her phone.

Dean picked up on the third ring.

“Hey, Cassie.”

“Dean… Can you meet me at the park? We need to talk.”

“Uh oh. Am I in trouble?” He joked.

“No. Nothing like that. I’ll see you soon.”

When Cassie confronted Dean, he finally came clean about everything. His dad was an alcoholic who spent all their money on booze and gambling. Sam left when he turned 16 and Dean hadn’t heard from him since. Dean’s mom burned up in a terrible fire. And Dean lived in government assisted housing with his dad. Dean was ashamed of his life, his family. He thought Cassie would look down on him if she knew.

Cassie was a little hurt that Dean could think that of her, but she understood so long as Dean promised never to lie to her again, which he was all too happy to do. He did not want to lose her.

Other than that, their relationship was pretty great. On their one year anniversary, Dean asked Cassie to move into an apartment with him. She said yes. 

They were happy. The life they’d built for themselves was full of love and trust and mutual orgasms.

And again, Dean really loved Cassie. She was the best thing that ever happened to him in his miserable, worthless life. He dreaded the day when she realized she could do way better than a highschool drop-out with massive Daddy issues and a severe case of emotional repression.

Dean knew all of this to be true. So why couldn’t he stop thinking about his new neighbor from across the hall?

It all started when the guy moved in. Dean was on his way out for work when he got a text from Sam about getting together for drinks this weekend. Which is why he was looking down at his phone instead of in front of him like he should have been. He was completely unaware of the guy with a massive view-obstructing box coming down the hall. They collided rather hard into one another, sending the box out of the guy’s hands and spilling its contents all over the dark gray tile of the hallway. Dean let out an “oof” from the impact as it knocked the wind out of him.

The contents of the box went everywhere, like a silicone explosion. Dean did not notice at first. He was too distracted by the man’s sharp jawline and incredibly blue eyes. He was unusually attractive, for a guy that was. Not that Dean spent much time assessing the physical attractiveness of other men. There was also a barely visible pink hue quickly forming on the guy’s cheeks, and he wore quite a sheepish expression. Dean raised an eyebrow before following the man’s eyeline to the contents that were previously in the box: a rather large assortment of dildos, buttplugs, leather restraints, and several other things Dean was uncertain what their intended purpose even was, but he knew enough to know they were more or less sex toys… kinky sex toys. Dean was hardly a prude, but he kept away from the weird shit like nipple clamps or spreader bars… then again… he might be persuaded-

“Oh, shit.” Dean exclaimed smartly, watching the other man quickly stoop to collect up his things. “Here, let me-” The words died on his lips when the guy looked sharply up at him. Clearly this was not the time to be polite and offer to help him gather his things. Dean cleared his throat. “I mean.. Let me go get something for you to put these in... That box is busted.”

“That is not necessary.” The man protested with a gruff voice much deeper than Dean expected. The guy sounded like one of the cowboys in the westerns Dean watched over and over as a teenager (and as an adult, don’t judge). He kind of looked like one of the heartthrob characters too. You know, the ones they threw in for the ladies (or fellas, Dean didn’t judge either) to enjoy.

“Come on,” Dean plastered on his best charming smile, partially just trying to put the guy at ease in this embarrassing situation. “It’s the least I can do. Plus, if you don’t have something to carry all this stuff in, you’ll have to carry it down the hall a handful at a time. Anyone else could walk by and see…”

The man let out a long suffering sigh. “Fine.”

Dean stood motionless for a moment before his brain caught up with him and he jumped into action, speed-walking back to his apartment and fumbling with the keys attached to his lanyard to unlock the door. Approximately 30 seconds later by the man’s count, Dean came back with a beaten up old laundry basket that looked like it had survived World War 2, or at the very least, the Reagan administration. The man shuddered at the thought.

“Ah yes. This will be discreet.” 

Oh, so Dean’s new neighbor was a little sassy. Interesting. 

Reluctantly, he took the basket from Dean with an exasperated “thank you,” which he said after a moment’s pause, as if remembering too late to be polite.

“No problem, man. It’s my fault. Should’ve watched where I was going.” Dean replied. His hand moved to rub that back of his neck, a nervous habit he had developed in his teen years when he was always embarrassing himself with his inability to stop words from escaping his lips. He would find out in adulthood that it was at least partially attributed to undiagnosed ADHD. “I’m Dean by the way.” He held out his hand to offer a handshake, aborting the gesture when he realized the guy’s hands were currently otherwise occupied… with dildos that he was collecting to put in the basket.

“Cas,” said Cas. Not a man of many words, Dean mentally noted. 

“Cas… Is that uh, is it short for something? Like Cassidy or Casper?” Dean asked, more for the benefit of making himself laugh than anything else.

Cas did not spare a glance up at Dean as he collected the last of his things. He really did have an impressive collection of sex toys. A bright purple tentacle-like dildo caught Dean’s attention and he struggled to form any thoughts beyond the utter surprise at having learned so much about a man he just met. The image of this man using the dildo on himself flashed before Dean’s mindseye and he shut that shit down real quick, but not before it got his pulse stuttering just a bit.

Was it warm in this hallway a moment ago?

“Castiel.”

Dean’s dangerous rabbit-hole train of thought was interrupted, causing him to blink hard and clear his throat. Castiel was looking up at him now. Those blue eyes made him feel exposed… Seen.

“Castiel?” Dean asked with an almost-rude tone of disbelief before he could stop himself. “That’s kinda unusual.”

Castiel bristled and stood up, that crystalline blue gaze turning scalding. His knuckles had gone a little white from the grip he held on the basket, supported by his hip.

This Castiel guy had some kinda very large hands, Dean’s mind noted without his consent or say-so.

“Yes. Castiel. Now, if you’ll excu-” 

“So you’re moving across the hall?” Dean blurted, although he was not entirely sure why he did so.

Castiel just grunted in a way that could either be from amusement or annoyance, but he nodded in confirmation. Dean wasn’t quite sure if the guy didn’t like him or was just embarrassed by his closest neighbor getting a good long look at his entire sex toy collection. Maybe both. Probably both.

“Cool, cool. I live right here,” Dean gestured to his door, “with my girlfriend Cassie who you’ll probably run into one of these days… hopefully without the dildos next time. Heh.” He smiled to himself, obviously amused by the thought of Cassie happening upon Cas in this very scenario. Cassie would get a hoot and a half out of this.

“I will return your laundry basket to you soon.” Cas said. “I have to go now. Bye.” And with that, he turned on his heel and walked away.

What a weird and interesting little guy.

That night when Cassie got home from work, Dean grabbed her by the waist as she walked into the kitchen and pressed an open-mouthed kiss onto her neck.

“Hey, baby.” Dean hummed, nosing at her cheek like a cat pleased to see its owner. In response, Cassie smiled and tilted her head to the side, enjoying the feeling of her boyfriend’s lips on her skin.

“Hi, handsome.” She chuckles. It was a beautiful sound, warm and delicate, much like the woman herself. “How was your day?”

Dean pushed Cassie back until she was leaning against the counter and pressed his hips against hers, seeking friction for the situation in his pants that was resolutely making itself more apparent with every passing second. He moved his hands up to cup her face and kissed her long and slow. His tongue sought out the seam of her lips, prompting Cassie to open up so Dean could lick inside like it is what he was born to do. 

Dean loved kissing Cassie. It was always good, always hot. Dean could be dominating the kiss in one second and just trying to hang on for the ride in the next. Cassie loved to give as good as she got and Dean loved it when she did.

Cassie sucked on Dean’s bottom lip and ran her hands up under the front of Dean’s shirt to feel up his chest. Her acrylic nails scraped so lightly along Dean’s chest that it kind of tickled, grazing ever so slightly over one of Dean’s nipples causing his breath to quicken just a bit. She pulled back from the kiss just enough to look into his hooded eyes, which opened curiously at her movement. They stood there for a moment just breathing each other in.

“Dean…” Cassie whispered, touching her forehead to Dean’s. “Sweetheart, what do you need?”

Although he would never admit it, Dean made a soft, desperate sound as his hips ground forward, pressing his erection into her hip. He dropped his forehead to her shoulder and stayed there like that for several moments.

Cassie understood. She always did.

“I… uh.” Dean began. “I want you to…” He mumbled the last bit, which Cassie couldn’t quite make out. However, she did not really need to. She always knew what Dean was thinking. It was honestly a little freaky sometimes.

“ Oh. ” was her smug response. “I know what you need.”

Dean’s head shot up and his molten gaze met hers. He let her take his hand and lead him into their bedroom. She had such delicate hands for someone who could so effortlessly make Dean fall apart under them.

Their shared bedroom was nothing too impressive. Neither one of them was great with interior design. But it got the job done. There was a bed, of course, with a stack of fluffy pillows and a very soft hunter green comforter that Dean picked out himself when they first moved in together. On either side of the bed were nightstand tables from Ikea that Dean put together with Cassie’s supervision. The room also had a dresser and a full length mirror which faced the bed. That was Cassie’s idea. They both enjoyed watching their reflections during sex. Dean used to think that kind of thing was too weird, but it took very little convincing from Cassie once she explained exactly how much fun it could be. Aside from the mirror, the walls were mostly bare except for a few tacky pieces of abstract art Dean picked up from TJ Maxx. If he squinted, they kind of looked like naked bodies, which was half the reason Dean decided on buying them. The other half was because they were on clearance.

Cassie maneuvered Dean to stand at the end of the bed, which was not hard to do. Dean loved to be pushed around. More than any heterosexual man ought to if Dean was being honest (which he rarely was about these things). Cassie pressed her hand to Dean’s chest and his knees folded as he sat down on the comfy memory foam, green eyes never leaving her warm brown ones. Cassie turned away from Dean and walked with purpose over to the dresser and dug through the top drawer until she found what she was looking for.

“Take off your clothes for me.” She said over her shoulder, not even checking to see if Dean followed her direction. She knew he would. Eagerly.

Dean did not pay much attention to what Cassie was doing as he undressed. He knew exactly where this was heading. This was far from the first time. Once Dean was fully bare, he returned to his seat on the bed, his erection standing proudly in view for Cassie to see when she finally turned back to face Dean.

“Sometime tonight might be nice,” Dean mumbled, mostly to himself.

Cassie just laughed sharply. She knew this bratty attitude would not last. It never did once they got started.

After an eternity (about three minutes), Cassie did turn around to Dean’s relief. His eyes slid down her body and caught on two thick black straps wrapped around her now bare hips. He felt himself start to salivate at the sight of the bright blue dildo that jutted out in front of her, attached at the base to the straps. The silicone appendage was not unlike some of the toys Dean’s new neighbor owned, Dean definitely did not note to himself.

There was just something about the way Cassie confidently wore a strapon that got Dean’s engine going. Never before had he met another woman who knew how to wield an erection quite like Cassie. Rhonda Hurley was a close second, but Cassie blew all the competition out of the water. She just knew exactly how to leave Dean trembling with a wonderfully sore ass. It sent a thrill through him whenever he felt the aftereffects days later. He got to walk around in public, carrying the knowledge of that deep ache without anyone being the slightest bit aware.

Dean took a deep breath and closed his eyes for a moment to process the sight before him. This was not the first time he had seen Cassie like this, but it still turned him on like nothing else.

Aside from the gloriously beautiful strapon she wore, Cassie was completely bare of clothes. Dean wanted to get his mouth on her body wherever she would allow. He loved hearing her appreciation at the attention he gave her. He loved knowing he was pleasing his partner.

“Get on your hands and knees for me, sweet boy.” She brooked no argument with her firm but gentle tone. Fuck, did that tone do things to Dean. He obeyed with plenty of enthusiasm, causing her to give an amused hum. He heard her walk toward him and felt the bed dip. His arms broke out into goosebumps in anticipation.

Cassie’s hand stroked down the flank of Dean’s back. She smacked the meat of his ass just enough to sting and force a surprised, but not displeased sound out of Dean. Her hands roamed back up to his shoulders, followed by her body pressing against his back. Her nipples were hard. Her strap brushed against Dean’s balls from behind.

Dean took a breath to calm himself.

“Turn around and face the mirror, sweetheart.” She whispered in a low voice right next to Dean’s ear, causing a shiver to run down his spine.

Cassie pulled away and waited for Dean to get into the position she deemed best for tonight, resituating herself behind him once again. 

Dean made eye contact with himself in the mirror, which always embarrassed him quite a bit and turned him on in equal measure. He heard the pop of a cap and saw the reflection of Cassie’s smile behind him. That was all the warning he got before he felt a cold, slick finger slide over his hole. For several seconds, Cassie just kept up the teasing, pressing in the tiniest bit every so often, but never enough. Dean clenched around nothing and huffed out a breath.

Cassie decided she would finally take mercy on her sweet boy by adding some more lube to her finger and carefully, slowly pressing it into the warmth of his hole. She attentively fucked her finger in and out for a bit to get Dean used to the intrusion before pulling out to pour more lube onto her fingers. When she pressed in again, this time with two fingers, Dean fell forward from his hands to his elbows and ground his hips back in an attempt to get her fingers on his prostate. She scissored and stretched his hole, then pulled out for more lube. She was nothing if not painfully thorough… and enjoying every second of this torture.

“Cassie…” Dean groaned, dropping his forehead to the mattress. He was several seconds from breaking out into a sweat. Need thrummed under his skin causing Dean to feel like he was vibrating. After several more minutes, Cassie added a third finger and began to actually give Dean some pressure on that bundle of nerves just inside his hole. She curled her fingers down and Dean let out a filthy moan when she rubbed against his prostate properly.

“You’re doing so well for me.” Cassie practically cooed from behind Dean. “You’re so wet, aren’t you?”

Dean grunted in agreement, feeling his face heat. He never knew how to handle praise, or for that matter, how to handle Cassie’s dirty talk that bordered on… something else. He did enjoy it though, despite his embarrassment. Perhaps he liked that too… just a bit.

“Are you ready for my cock, Dean?” Cassie asked without really asking. She knew the answer. It was more for the needy reaction she knew it would elicit from her boyfriend. “Ready for me to fill you up? Make sure you know who you belong to?” She withdrew her fingers, causing Dean to huff in disappointment. He heard the slick sound of more lube on silicone and then felt the head of the dildo rub against his thoroughly prepared entrance. 

“Oh, god. Please. ” Dean breathed out on a sigh, attempting to push his hips back, but Cassie just withdrew her dick from his hole for his trouble. He was not calling the shots.

“What was that?” Cassie asked with a devious smile on her lips. Dean could not see it, but he knew it was there. She had Dean exactly where she wanted him.

“Please…” Dean’s face was flushed with warmth from the desperation he felt. “I need… I need. ”

“What do you need, Dean? I want to hear you say it.” Cassie spoke firmly in a way that went straight to Dean’s neglected, leaking dick. He bit his lip in frustration.

“I- I…” Dean squeezed his eyes shut and took a deep, stuttering breath. 

“Dean, look at your reflection and say it. I want to hear my boy tell me what he needs while he sees just how desperate he is.”

“Jesus…” Dean shudderied and reluctantly peered at his reflection once again. He was a vision, truly. On his elbows, ass in the air, body flushed and gleaming with sweat. He really was desperate. 

“ Please fuck me, Cassie. I need you inside me. I’ll be so good. Please- I just- I need- fuck, Cass… I need it. Need you.” Dean was babbling and whining and if he could hear his own words outside of his aroused state, he would be burning up with shame. But at this very moment, he could no longer stop the words pouring from his lips even if he still wanted to. He could practically hear the amusement and arousal in Cassie’s voice when she told him how good he was for asking for what he wanted. She was basically purring through her praise. He did not have to wait much longer before she was pushing her hard-on into Dean’s hole, causing him to groan in pleasure and thank any deity, god, angel, whatever the fuck who was listening that he was finally getting what he desperately needed. He was only given a moment to adjust before Cassie started moving her hips, picking up a rhythm that was driving him slowly to insanity.

The sight of Cassie’s reflection thoroughly wrecking Dean was intoxicating. The stretch and the fullness of the dildo felt so good. And the way it rubbed up against his prostate on every thrust was incredible. Dean would never understand why any man would not want a cock up their ass if it took them this close to feeling heaven.

As Cassie picked up her speed, hips pounding into Dean just right, she reached around to stroke his cock finally in time with her thrusts. Dean pushed back into the thrusts with the conviction of a man possessed to get all the pleasure he could from her. Cassie used her free hand to grip Dean’s hip in a way that made him feel like he was being pulled full-body back onto her length. He had no idea how a woman so much smaller than him could command his body with such ease. Dean whined so loudly it would be embarrassing if Cassie were not currently fucking his brains out through his asshole. He was so close. He just needed a little more of a push.

“You’re such a cockslut, aren’t you, baby.” Cassie marveled. “You’re taking me so well. So wet for it. Almost like you’re made for my dick… Fuck, baby one of these days you have to let me handcuff you while I fuck you.” There was a hint of a growl in her voice, just enough to take Dean’s mind elsewhere.

A flash of blue velvet handcuffs came into Dean’s mind. The handcuffs that had fallen out of their new neighbor Castiel’s sex-toy box. Christ, the guy owned so many toys. Dean wondered if he used all of them on himself when he was alone, shoving a thick blue vibrating dildo up his ass, or if he used them on his partners. He would probably handcuff some lucky lady or fella to his headboard and then edge them with a vibrator until they were frantically babbling and in tears, pleading with him for their release. That gravely voice would soothe said person as he told them they just had to survive one more round getting right up on that edge and then they could come. Once they completed, he would tell them exactly how good they were for him, how they were just perfect at following his orders.

“So good for me.” Cas would say. “So good… Dean- ”

Before Dean even realized where his thoughts strayed, he was tumbling over that edge himself. He moaned brokenly as he shot his release, hot and sticky, onto their nice green comforter. They forgot to put down a towel, thought Dean absently. He collapsed onto his stomach and attempted to catch his breath. A soft hand ran up and down his back, but he was too busy floating on happy chemicals to process much else. Distantly he heard the thump of Cassie’s strapon hitting the floor and then the click of a lamp being turned off before he felt a warm body curl up next to him. At some point Cassie must have cleaned Dean up with a wet cloth as well because he did not feel sticky anywhere.

“I met our new neighbor today.” Dean mumbled, almost unintelligible. His mouth was partially muffled by the pillow.

“Yeah?” Cassie sounded amused. She loved when Dean got blissed out like this. “Across the hall?”

“Yeah. Some guy named Castiel. Nice dude. Big sex toy collection.” Dean didn’t stay conscious long enough to observe a reaction from Cassie. He is not sure what he would have seen anyway.

Chapter Text

The morning after Dean and Cas had their rather awkward hallway meeting, Dean was off work for Memorial Day, but Cassie still had to go in because the news never stops or something like that. Dean decided that he would be a friendly neighbor and bake some cookies for the new guy across the hall. He pulled out all the ingredients he would need before realizing that he had no sugar. The brilliant idea to borrow some sugar from his neighbor popped into his head. Before Dean could even think about what he was doing, he was knocking on Cas’ door, empty sugar container in hand and half-mixed ingredients abandoned on the counter.

Dean stood there for about twenty seconds before he started to suspect Cas might not be home. He was proven wrong when Cas finally opened the door in only a towel. Dean’s eyes widened and he quickly lifted them to make eye contact with Cas instead of looking… elsewhere. 

“Can I help you?” Cas squinted in confusion at Dean. His hair was wet and messy. It looked kind of nice.

Dean wasn’t staring. He definitely was not looking anywhere, actually.

“Hi, man. I’m here to bake cookies.” Dean blinked hard as he processed what he just said. “I mean… I’m baking cookies and I need to borrow sugar… if you have some, I mean. Do you?” He finished lamely with an awkward smile, clearing his throat.

Cas just looked back at Dean for a moment. The guy could be alarmingly still. Like a statue. He was quite… statuesque. Especially considering the miles of skin currently on display. His towel was slung low on his hips and he was one gentle tug away from becoming Michaelangelo’s David . 

“I think I have some in one of the boxes marked ‘kitchen stuff’” Cas punctuated with finger quotes, “but I’m still in the process of unpacking. I’ll have to search for it.”

“Right.”

Cas looked at Dean expectantly. “Were you planning to come in or were you waiting for someone to walk by and see me in this state so you aren’t alone in having intimate knowledge of me?”

If Dean’s mind could audibly screech to a halt, Cas would undoubtedly hear it. Hell, he might even be able to see his words land with impact just from Dean’s facial expression.

Without another word, Cas turned and retreated into his apartment, leaving Dean to trail after him and take in the sight of all the boxes littered throughout the apartment.

“Dude.. you have a lot of shit for one guy.”

Why did Dean have to say something so borderline rude, you ask? Good question. He couldn’t tell you. It just kind of slipped out as things often did. Dean admittedly did suffer from the occasional foot-in-mouth syndrome. He would say it’s genetic, but he is almost certain it stems from his very poor impulse control.

“I went through a break up recently and my ex wanted a fresh start, so I was left with all of the furniture and extraneous items we bought together.” Cas said as he waltzed into the bedroom, leaving the door cracked.

This time Dean did not follow.

“So I take it he broke up with you?” Dean called after him.

If nosy were a person, it would be Dean Winchester. He loved hearing about the good, bad, and embarrassing shit in people’s lives. There was something especially interesting to Dean about Cas’ personal life considering Dean knew quite personal details about the other man, but not his last name or what he did for work. Hell, Dean didn’t even know if Cas liked men or if his dildo collection was just something kinky thing like what Dean had going on with Cassie.

“No.” Castiel responded flatly after a moment. “I broke up with him ,” he added as he came back out from the bedroom, fully dressed this time.

Cas looked quite cozy in a faded Taylor Swift t-shirt and dark gray sweatpants that fit him nicely.

“Oh.”

Dean suddenly found his surroundings very interesting. Cas’ apartment was pretty much the same as Dean and Cassie’s place, but it had a door to a balcony. Dean thought he wanted a balcony when they were first apartment hunting, but the price difference did not seem worth it to Cassie, so Dean decided balcony life was not for him. Now on the rare occasion that Dean did decide to partake in a few cigarettes to soothe his nerves, he had to take a trip out to the parking lot. It was for the best in the end because Cassie really hated the taste of cigarettes on Dean’s tongue.

Cas took Dean’s wandering eyes as his cue to start his little scavenger hunt. He looked around on every surface in search of something and let out a little triumphant noise when he found what he had apparently been looking for: a boxcutter. Armed with his new tool, he started cutting open boxes that were in the stack nearest the kitchen.

“Need any help?” Dean offered. He was feeling a little useless just watching the other guy hunt for what Dean needed.

Castiel just ignored him and kept digging through boxes. The man was on a mission now. His brow was furrowed in focus on his singular purpose. It was honestly a little too intense for something so benign, but Dean found himself amused all the same.

“You know, if you’d labeled those while you were packing, it’d be easier to find things.”

Cas paused and looked up at Dean, tilting his head. The look he gave was clearly one of equal confusion and annoyance. He looked like one of those grumpy puppies you see in memes on facebook that go along with a caption like “when your owner doesn’t understand that it’s playtime” or something equally as cringeworthy. It was kinda cute.

Not that Dean was thinking about the endearing qualities of a man whose dildo collection was well known to him… 

Dean really needed to stop fixating on that.

“Yes, that would have been helpful if I had not been given a four hour window to ‘come collect my shit’ because I was ‘no longer welcome in the apartment.’” There were those finger quotes again. Who was this guy and what cheesy 90’s sitcom was missing their loveable, yet-gruff and out of touch, nerdy professor character?

In truth, Dean’s mind had already hopped, skipped, and jumped away from what he said to prompt Cas’ slightly miffed reaction. Oh right. Labeling boxes. Ha.

“Ah.” Dean sucked in a breath. “Geez, buddy. What did you do to the guy?”

Cas looked up at Dean and replied very seriously, “Ishim wanted to bring a third person into our bedroom and I was not comfortable with that.”

“Shit…”

Castiel moved to resume his search, but stopped again to continue his explanation. “And despite the numerous conversations we had about it in which he told me he would accept whatever I was comfortable with, he still pushed me to go through with it.”

Dean made a sympathetic noise. “Yeah I could see how that would be difficult.” He internally berated himself for making the other man divulge something so personal so soon after their meeting, nosy nature be damned.

After several more boxes were opened and rifled through unsuccessfully, Cas finally pulled out a little sack of sugar. His demeanor changed to one of satisfaction at having found what he was searching for.

Dean took the sugar and the hint to change the subject. His fingers grazed against Castiel’s, causing him to almost drop the sugar container. That would be Dean’s luck given his track record with this man. Thankfully, Cas’ reflexes were a little better this time around, catching the sugar before it hit the ground.

“Thanks, buddy.” Dean grinned, successfully taking his prize this time.

“You said you were baking cookies?”

“Yeah.” 

They stared at each other for a moment. Or several. Dean could not keep track, in all honesty. He got a little lost.

“Would you mind terribly if I helped?” Castiel tugged on Dean’s wayward-loving heartstrings with his warm, blue eyes. If Dean wasn't careful, he could get lost charting the constellations he found there.

Dean had a feeling this was somehow going to be a terrible idea.

“Yeah… I mean no. Not at all. Come on over, buddy.”

Castiel’s smile in response was pleased.

The smell of sugar cookies cut into the shape of cowboy hats and boots filled the apartment. Don’t ask Dean how you could smell the specific shape of the cookies. This was already a moot point that Dean and Cas argued about good naturedly for several minutes after the smell of cookies started wafting their way. During their baking session, which turned out to be less of a group activity and more of Castiel watching while Dean did all the work, Dean learned more about his strange and intriguing new neighbor. And he supposed his new neighbor learned more about him in turn.

Dean learned that Cas was the youngest of three children, that he was recently hired as a Gender and Sexuality professor at the local college, that he had a strange affinity for bees, and that he was incredibly adorable. That last fact was not something he learned by asking Cas. He figured that one out all on his own.

“So where do you work, Dean?” Castiel asked after several long seconds of Dean staring dumbly at Castiel for sharing what his occupation was. Dean was still processing the fact that there was such a thing as a gender and sexuality professor - and in Kansas of all places…

Dean blinked and glanced over his shoulder to the timer sitting on the counter, which told him they still had quite a while before the cookies were ready.

“I’m a mechanic. And I restore classic cars when rich old people shell out the cash for it.” Dean answered and shifted his position leaned against the counter so he was not facing Cas directly.

Castiel seemed impressed although Dean had no idea why. Working under the hoods of old clunkers getting grease stains under his fingernails did not exactly seem like something a college professor would find impressive or interesting. Although it was what Dean loved to do, he knew how these intellectual types looked down on manual labor and blue collar workers. He had met enough of Sammy’s lawyer friends to know.

“So you’re good with your hands,” Cas mused absentmindedly, an innocent smirk on his face. Which should be an oxymoron, but on this guy, the smirk somehow seemed genuine.

Dean coughed for lack of a response coming to him and then he chuckled nervously.

“Sorry,” Cas seemed to realize the suggestion in what he said, shifting his weight from one foot to the other. “I just meant- I’m- I think it’s important. You know, having a valuable skill like that. If your car breaks down on the side of the road, you can fix the problem without having to call anyone. If I am stuck somewhere, I can’t exactly argue the validity of neopronouns with my vehicle to get it running again.” He snorted, seemingly amused with what he said.

“Sure…” Dean nodded along like he understood, meanwhile he was thinking “ What the fuck is a neopronoun? ”

They found themselves in a bit of an awkward silence after that. Dean checked his phone for lack of anything else to do with his hands and saw another text from Sam. It asked if Dean wanted to meet up at the Roadhouse for a few drinks with Sam and his lawyer friends after they got off work. Dean groaned at the thought of having to put up with those pretentious dicks. Dean loved his little brother, but he had no idea how such a sweet and caring kid ended up with such obnoxious friends.

Castiel noticed Dean’s distress and cleared his throat. “Did you receive an upsetting message?” 

Dean glanced up at Castiel who looked very earnestly concerned. It was only a little endearing.

“Huh? Oh.” Dean’s lips quirked up. “Just my little brother.”

“You don’t like him?”

“No, it’s not that.” Dean sighed. “He just invited me out with him and some of his buddies and they aren’t my favorite people to be around.”

Castiel’s eyebrows furrowed and he nodded in understanding. “Your brother has made a poor choice in companions.”

“Totally. A bunch of snotty legal types who think because they have esquire behind their name that they’re hot shit. I’m sure you know how it is, given that you’re one of those academic types.” Brain catching up with mouth, Dean mentally smacked himself. “I mean- not that you are that way. Just… I’m sure you work with academic snobs all the time. You though, you… you seem pretty down to earth from what I’ve gathered. Not snobby at all. Very… not… dickish?”

The corners of Castiel’s lips ticked up in a gentle smile. “Thank you, Dean. I do know what you mean. Some of my colleagues do seem to hold the idea that their degrees give them the right to condescend to whomever they please.” He gave a long suffering sigh.

“You wouldn’t want to come with me, would you?” Dean found himself saying before he could even think too hard about it. “It’s just- I mean, you could be like a buffer. You know, Sammy and his friends and me and my…” Neighbor whose sex toy collection I am overly familiar with. 

“New friend,” is what Dean settled on.

“I would like that. In all honesty, I rarely go out if it isn’t for work.” A look Dean couldn’t quite discern passed over Castiel’s face for a moment. It seemed a little lonely, which made sense considering Castiel’s recent breakup.

“Well, great!”

“Great.” Cas agreed warmly, holding Dean’s equally balmy gaze.

The timer dinged, causing Dean and Cas to jump slightly.

“I should get those.” Dean rushed to the oven, putting on his “Blow the Cook” mitts (Cassie’s Christmas present for Dean last year) and pulling the cookie tray out of the oven.

Castiel followed after Dean, standing just a little too close to Dean for comfort, and inhaled the delicious aroma of cookies. “Those smell incredible, Dean.” Cas groaned in delight.

Dean let out a startled laugh and thanked Cas.

“What are these for anyway? There are quite a lot of cookies for just you and your girlfriend.”

“I didn’t tell you, man? I made these for you as a sort of welcome to the neighborhood gift.”

Cas paused, looking taken aback. “Dean… I’m touched. I can’t think of the last time someone did something for me just to be welcoming.”

“Whatever. It’s nothing really.” Dean scoffed at the thought that a man like Cas would not have dozens of people falling over themselves to make Cas feel welcome in all kinds of ways.

“No, I really appreciate the thought.” 

A tingly feeling made its way through Dean’s body, but he wrote it off as getting a little overheated from the oven subtly warming the whole kitchen just a bit.

Dean spent the rest of the day cleaning around the apartment and doing laundry, waiting for Cassie to come home. Most people would never guess based on Dean’s personality, but he was actually a bit of a neat freak. He was a firm believer in preventative cleaning and the idea that everything had its own place. Cassie was by no means messy, but she knew Dean was very particular about how he kept his space, so she usually just left the cleaning to him. Dean preferred it that way.

When Cassie walked through the door, she took in the smell of burgers and fries that was coming from the kitchen. It smelled heavenly. She loved coming home to a nice meal and a loving man. Truly, Cassie had never been so happy as the two years she had been with Dean. They just fit so well together. They each had their own strengths, which made up for the other’s weaknesses.

“Honey, I’m home.” Cassie called, taking off her coat and hanging it neatly in the hall closet the way she knew Dean preferred. 

In all honesty, Cassie used to be the type who would come home, kick off her shoes, throw her coat over a chair, and pass out on the couch. Since moving in with Dean, however, she developed new habits out of necessity. She was aware how much it stressed Dean out when things weren’t in their proper place. Sure, he loved to clean, but Cassie knew it was more for the result than the action itself.

Dean stuck his head out of the kitchen and grinned, yelling a quick greeting before returning to what he was doing in the kitchen. Cassie followed him, walking up behind Dean and snaking her arms around his waist. She pressed a feather-light kiss behind his ear.

“All this for me, handsome?” She hummed with self satisfaction when she felt him shiver.

“You know it.” He replied, setting down his spatula to place his hands on Cassie’s smaller, softer ones.

A little while and an orgasm or two later, Dean and Cassie sat at the dinner table, ready to chow down on the meal Dean worked hard to prepare, when they heard a knock at the door. Cassie kissed Dean on the cheek and slid out of her seat to answer while Dean stuffed his face with fries and kept an ear out for whoever might be at the door.

“Hello,” came Cassie’s sweet, slightly confused voice. 

“I hope I am not coming at a bad time.” came the unmistakable timbre of their newest neighbor Castiel. “I’m here to return this.”

Dean practically leapt out of his seat to come stand behind Cassie at the door.

“Castiel!” Dean exclaimed cheerfully. “Babe, this is the new guy across the hall I told you about.”

“Oh, right.” Cassie replied with amusement, seeming to be sizing Castiel up. “The one with all the sex toys.”

Castiel blanched at that. He still looked good despite the color leaving his face. Dean would not admit to giggling in response. 

Castiel elected to breeze past Cassie’s comment, most likely to preserve any dignity he had left. Instead he just held out the laundry basket in offering, which Cassie gladly took from him.

“Castiel, please come in. We have extra burgers if you’d like one. Dean is an excellent cook.” Cassie’s tone, though light, did not broker any arguments. She turned and walked past Dean, not even looking back to see if both men were following behind her. “And I’d love to get to know you a little better.”

Dean and Cas shared a look. Cas had a bit of a deer in headlights look and Dean threw back a “what can ya do?” face. Knowing there was no choice, they both trailed after Cassie.

Chapter Text

Castiel loved Ishim. The effortless confidence he possessed. The way he commanded a room. His silvery voice. The way he made Castiel feel like he was the only person in the room. Like he was special and attractive. As their relationship progressed, these would be the same things that turned Castiel off of Ishim. Confidence melted down and reformed into arrogance. His ability to command a room was actually overbearing and far too forceful. His silvery voice became a silver tongue that could manipulate Castiel in ways he could not possibly discern or avoid. Ishim still made Castiel feel like he was the only other person in the room, but instead of a soft glowing focus, it was a harsh spotlight to point out his imperfections. Castiel no longer felt special and attractive. Instead he felt like the odd one out and like he was loved more for his appearance than his personality. 

Suffice it to say, Castiel had been looking for a reason to leave, which Ishim finally provided by pushing Castiel just a bit too far. Ishim was great at pressing against boundaries until he got what he wanted, but this final time he had not been expecting Castiel to finally snap. Castiel himself had not fully expected it either.

It was a Friday like any other, a little tiring considering Cas spent most of the day teaching lectures and dealing with varying levels of annoyingly needy students (which he enjoyed, mind you, but it still became tiring at a certain point), but it was a fairly mundane day. 

When Castiel got home, he expected to find his boyfriend either preparing for his upcoming presentation for work, or taking a nap on their bed as he was prone to doing after a long day. Instead, when Castiel saw the living room was empty and went to check the bedroom for Ishim, Castiel found something he definitely did not expect: Ishim and some coworker of his whose name Castiel could not be bothered to remember right now… naked. In bed together.

The sound of Castiel opening the door alerted the two men to the fact that they had company. 

Ishim pulled off of what’s-his-face and rolled onto his back, throwing a smarmy grin in Castiel’s direction.

“Castiel, you’re home early.” Ishim punctuated the greeting by fisting his cock and grunting… He was getting off on this. “You remember Theo from the office potluck last month?”

Castiel was trying valiantly to take deep breaths so as not to walk across the room and smite Ishim right there in his fury.

“He’s a little present for you.” Ishim said, either not seeing the very obvious anger radiating from his boyfriend or choosing to ignore it. “I got a little distracted and decided to get the fun started early… Can you forgive me?”

This must have been a dream of some kind. Or Castiel had finally lost the fragile tether with which he held onto his sanity because there was no possible way this was happening to him. They had discussed this exact thing in depth multiple times. Ishim knew Castiel was not comfortable with a threesome and he thought he could just make it happen anyway.

There was no argument after. Normally this kind of thing would prompt a weeks-long yelling fest that ended with admittedly enjoyable make-up sex, but this time Castiel was done. He wanted nothing to do with Ishim any more. So he packed up his meager possessions and showed up on his brother Gabriel’s doorstep like some lost puppy.

Ishim, being the kind of man that he was, began his tour of self-victimization, telling all of their mutual friends, Castiel’s co-workers, hell even Castiel’s family, that Castiel was the one who cheated. Somehow Ishim seemed to hold the belief that this would bring Castiel back to him. Or maybe he just wanted to punish Castiel for finally having the balls to leave his sorry ass.

After a week away, Ishim called Castiel, telling him how sorry he was and how much he missed him. When Castiel rightfully told Ishim where he could stick his apologies, Ishim changed tactics, telling Castiel there were a few more of his things left in the apartment and if he wanted them, he would have to come get them at a specified time. 

Castiel knew he’d forgotten some of his clothes and a few things for work, so he had to play Ishim’s game if he wanted them back. When Castiel arrived back at his old place, he found his landlord was the one to answer the door.

“Mr. Novak. So glad you could make it.” The slimy British man gave a lascivious grin. “Since you’ve decided to terminate your lease early and your boy-toy isn’t answering his phone, I need you to get all your shit out by noon tomorrow or I’m sticking you with a hefty fee.”

Castiel felt his stomach bottom out. Ishim’s last parting gift was to royally fuck Castiel over.

…

Cassie interrogated Castiel through most of the dinner, asking him questions about his work, family, childhood, and even a few that were subtly trying to suss out what kind of sex toys Dean had been witness to in the hallway the previous day.

Castiel was good enough at side-stepping the slightly invasive questions, but he found that he really liked Cassie. She was charming in an effortless sort of way and she was remarkably perceptive, which made sense given her profession as a journalist as Cas had just learned.

Castiel could see why Dean would be attracted to a woman like this. Although, Cas had a feeling there was something different about their relationship dynamic than any other straight couple he’d befriended in the past, not that there were too many, in truth. But he couldn't quite put his finger on what it was.

When all three people at the table were finished with their meals and Dean started clearing the plates, Cassie decided to give the interrogation a break and volunteer some information herself.

“Dean tells me you’re a gender and sexuality professor.” Cas nodded in affirmation. “You know, I had a boyfriend in college who majored in gender studies.”

Cas saw Dean’s ears perk up through the archway to the kitchen as he looked back at the table with interest.

“He was a really progressive guy. Really into playing around with the traditional gender roles of our relationship.” Cassie said with a fond smile, clearly reminiscing.

Dean stepped back into the dining room, a sheepish expression on his face. “Babe, I don’t really think he wants to hear about that.”

“Oh I don’t mind.” Cas replied. He was honestly quite curious where this train of thought was headed. Cassie was an interesting woman who had absolutely no trouble speaking about things that other people might find inappropriate and Castiel honestly appreciated that. He was a bit of an oddball himself, after all.

Cassie’s gaze turned sharp and her focus landed back on Castiel like she had an agenda with her next statement. “He was the first boyfriend I ever tried pegging.”

Castiel’s eyes widened a bit in surprise, but he had no chance to really react because Dean started sputtering and his face turned a remarkably bright shade of red. Castiel tilted his head in confusion. Interesting. There was something there.

After Dean took a moment to calm himself, he took the silence he had caused to abruptly change the subject.

“So, Cas… are you ready to head out for drinks with me and my baby bro?” His voice was a little strained.

Cas took a moment to catch up with the topic shift. “Oh. I did not realize that was still happening since you never specified a time.”

“My bad, buddy.” Dean huffed out a flustered laugh.

Cassie seemed to go slightly rigid.

“You’re taking Castiel to meet Sam?” Her voice got slightly higher, but did not betray any particular emotion.

“Oh, yeah. I mentioned how I didn’t really like Sammy’s friends and Cas offered to come with me to make it less awkward.”

Cas felt his brow furrow as he quickly recalled the conversation from earlier in the day. Dean had most certainly been the one to invite Cas. Maybe Dean took Castiel’s agreement to tag along as some kind of offer? Either that or Dean was giving a slight fib to his girlfriend. Strange. Cas decided not to mention it. Best to keep out of other people’s relationships.

“Oh.” Was all Cassie said.

“So, Cas? You still in?” Dean inquired with his most charming grin.

“I’m still amenable.” Castiel said, confused on what just transpired between this couple.

…

When Dean’s car roared into the parking lot, Cas noticed the other man bristle out of the corner of his eye.

“Can’t believe I have to pay to park here.” Dean grumbled, mostly under his breath, but Cas heard anyway. “Stupid fancy yuppie bar-

“Dean, if it would make you feel better, I will pay for the parking.” Cas offered like the gentleman he was.

This gave Dean pause from the annoyance stewing in his gut and he half-turned to face Cas from across the leather bench of the Impala. 

“That’s alright, Cas.” Dean said with a soft, amused huff. “Just help me figure out how to pay on my phone and we’ll be good. I’m useless with technology.”

“I’m not sure how much help I’ll be, but I’ll try.” Cas agreed as they both exited the vehicle, walking over to the sign with the payment info. It was quite evident neither one of them was particularly proficient with technology, but after seven minutes and a lot of curses from Dean, they managed to figure it out. This led Dean to complain about the price to park for a few measly hours all the way from the lot to the bar.

The theme of the bar could only be described as “pretentious gray minimalism”. The place was rather spacious admittedly, with high ceilings and stone gray floors. The furniture was all either stainless steel, with the exception of a few modern-looking black couches strategically placed throughout the room to create what appeared to be “hang out” areas. There was a chandelier hanging from the ceiling that looked like something out of Star Trek, which Dean pointed out.

Dean and Cas both took in the space around them and shared a look that Dean would fondly identify as mutual disgust for the decor. In fact, Dean was just about to make some snarky comment about the bartenders looking like they had sticks permanently lodged up their asses when he laid eyes on Sam who waved him over.

“Dean,” Sam called with a warm smile, standing to greet his brother. “Who’s your friend?” The question was an innocent one and a fair one, but it still made the back of Dean’s neck prickle a bit for some reason.

“Sammy, this is Cas. Cas, Sammy.” Dean introduced with a tone that was only slightly stilted.

“It’s Sam.” Said Sammy as he rolled his eyes. “It’s nice to meet you, Cas. Happy to see my big brother isn’t incapable of making friends.” 

“Ha ha.” Dean said dryly. “Don’t let Sammy’s appearance fool you. He’s actually pretty smart.”

Sam snorted at this and gestured for them all to take a seat before he waved over the waiter to order another round of drinks and some beers for Dean and Cas.

Cas took in the three people across the table that were clearly Sam’s snobby friends. Directly across from Cas sat a beautiful brunette woman who was eyeing Cas up and down and not being subtle about it. The two men next to her both held equally superior airs about them like they knew they were better than everyone around them simply because they wore fancy suits.

“Cas, these are my friends from work.” Sam’s voice broke Castiel out of his appraising stare. If slimy, uptight lawyers had a look, it would be these three.. Not that Castiel was making snap judgements per se. He just knew Dean didn’t like these people, so he was wary. 

 “This is Ketch. He works in real-estate law. That guy over there is Mick Davies. He’s a senior partner at the firm, which is why we keep him around,” This prompted an eye roll from the dark haired man. “And this…” Sam gestured to the woman whose smile just screamed trouble. “This is Meg.”

“Hiya, handsome.” Meg said with a smirk. Her voice was a sultry, warm sound that Cas might actually be into if he liked women. “It is truly a pleasure to meet you.”

Castiel shot back a polite smile and glanced at Dean whose expression appeared to have darkened… Maybe he especially did not like Meg.

Sam proceeded to explain how he met Meg, but Castiel was no longer paying attention. He was sure they were lovely people… but in all honesty, he had already forgotten the first guy’s name and pretty much everything else Sam said. It’s not that he didn’t care… Okay, yes it is. But also, Cas was distracted by the fact that Dean’s thigh was pressed up against his. And not just in a slight, “I didn’t even notice” kind of way. No, it felt intentional. Cas adjusted in his seat, easing up on the contact, only for Dean to move closer and seek him out once again.

Cas tried several times to make eye contact with Dean to ask him a silent question about what the hell he was doing, but Dean seemed to be paying all his attention to Sam and his pals’ dry banter they had moved on to. And to Cas this meant that Dean was intentionally avoiding eye contact because no one in their right might would be that enraptured by several self-important lawyers (and Sam who seemed to be perfectly nice despite his choice in companions) chatting back and forth.

“So what is it you do, Castiel?” Sam asked with interest, taking a sip of his scotch or bourbon or whatever the hell he was drinking, Cas couldn’t tell.

So Cas explained his career to varying levels of confused expressions, meanwhile Meg seemed even more interested after having learned Castiel’s profession. About halfway through Cas’ explanation, Dean’s shoe started rubbing repeatedly against Cas’ ankle. It was a bit distracting, but Cas resigned himself to this odd behavior from his supposedly heterosexual neighbor. Plus, it honestly felt kind of good.

Drinks with Sam and his friends went on for a while longer before Dean and Cas decided to call it a night.

When they were back in the Impala, the silence lingered on for several minutes before Cas finally broke it.

“May I ask you a question?”

“You just did.” Dean knew he was being an ass. In truth, he was dreading this question. He knew he had moved beyond the boundaries of what normal friendships dictated, but he couldn’t stop himself. Meg was pissing him off and he knew that if he fought off her wandering foot, he could protect Cas from her most likely (hopefully) unwanted advances.

Cas rolled his eyes

“Go ahead.” Dean prepared himself for the question about his sexuality. He got himself ready to have to let Cas down easy.

“Does Cassie dislike your brother?”

Dean blinked. “Oh… No. It’s not that… It’s just a sore spot…”

Dear reader, you recall when Dean promised he would never lie to Cassie again? Well that promise- unbeknownst to Cassie- had come with a caveat.

You see, Sam moved out at 16 without telling anyone. That part was true. In fact, the only evidence he hadn’t been kidnapped was a note Sam left for Dean telling him he had to get away from their dad and would make contact when he felt like it was safe.

John Winchester was a difficult man. And Sammy was just as strong-willed. They bumped heads constantly, John always feeling the need to impart his ‘wisdom’ onto his boys and Sam always feeling like he knew it all and didn’t need to be treated like a child. They disagreed on everything. Politics, religion, sports, even what to have for dinner. These arguments would start out civil enough, but they would escalate to the point of screaming in each other’s faces, leaving Dean to try and play mediator. When John was a little too boozed up, he would get a little more physically violent. Dean refused to let John lay a hand on his baby brother, so oftentimes Dean would be the one to end up with a black eye or a split lip.

One day, Sam had decided enough was enough. So he packed up in the middle of the night while Dean was out smoking with some buddies. He was impossible to track down. Dean spent many nights in a panic, wondering if his brother was okay, if he was even still alive. 

Sam finally reached out about a year later on Dean’s birthday. He called from a payphone somewhere in Illinois and asked to meet up with Dean, but only if Dean promised not to tell a soul lest it get back to John. Dean, of course, agreed. There isn’t much he wouldn’t agree to if it meant seeing Sammy again.

For years after that, they met in secret. Dean would make up an excuse to John about going out of town to meet up with some girl and John would tell him to not knock anybody up. Dean even helped Sam pay for college while managing to hide the money from John who would’ve lost it all betting on whatever the fuck he gambled his money away on if he’d had an inkling that Dean made more than he let on.

It wasn’t until John decided on a whim to move down to Florida with his girlfriend Kate that Sam finally stepped foot back in his hometown.

That was when Dean had no choice but to come clean to Cassie about the secret he kept for Sammy all those years. It was complicated as hell, but Sam wanted nothing to do with his father and Dean respected that. He wouldn’t share the truth with anyone, not even Cassie, until he got the go-ahead from Sam. And he hadn’t.

Cassie said she understood, but Dean knew she didn’t really. She was fixated on the fact that Dean had promised no more lying. They did eventually move past it, but Cassie never really got over it. She never said anything, but she clearly got touchy when Sam was mentioned.

Dean explained this all to Cas and it felt like pouring out his guts onto the floor for Cas’ inspection, but it also felt kind of good to get it out. Like puking when you’ve had too much to drink.

Cas was quiet for a while after Dean laid out his life’s story on the supple leather seat between them. The response he finally settled on was, “Thank you for sharing that with me, Dean. I’m sure that couldn’t have been easy.”

And Cas had this warm, knowing expression that just made Dean feel at ease. Dean barely knew the guy, but there was just something about him.

Dean nodded and started the car. They didn’t say much else on the drive home, but that was okay. Neither one of them minded the silence.

Chapter Text

Tight, wet heat enveloped Dean’s throbbing cock as he gasped into a slightly more awake state than he was a moment ago. His eyes were still closed, but his brain was alert enough to know what was happening. His hands moved down to thread through dark, messy hair and pull just slightly. Not enough to hurt, but enough to hold on.

“Fuck, baby. That’s good.” Dean moaned as his hips bucked involuntarily in response to a very skilled tongue laving at the underside of his erection. He felt a slick finger brush against the outside of his hole and spread his legs wider to give better access.

That talented mouth pulled off with a slurp and Dean opened his eyes to make eye contact with his girlfriend.

“Do you like that, Dean?” A decidedly not-Cassie voice with rough, masculine tones said from between Dean’s parted legs. Blue eyes partially hidden by heavy eyelids peaked up at Dean and spit-slick pink lips hovered just above the head of Dean’s dick.

“Cas?” Dean meant to ask, but instead it came out as more of a broken moan. Cas took Dean back into his mouth and beep.. beep… beep…

Dean sat up ramrod straight in his bed, heart pounding. He looked around himself and his bed was completely empty aside from himself. He felt a warm wetness in his boxers, quickly cooling in a way that was far from pleasant. Dean had a wet dream… About Cas. A man. And he had come in his shorts like a fucking teenager because of it.

“Fuck,” Dean groaned and hit the off button on his alarm with much more force than necessary, as if he could take his anger out on the thing and somehow feel better. No such luck.

He rolled out of bed and walked stiffly into the bathroom to take a shower. Distantly, he heard the sound of Cassie humming from the kitchen. She was probably getting ready to start her day while Dean was having wet dreams about the blue-eyed man who lived across the hall. He turned the water temperature in the shower as cold as it would go.

When he was dressed and ready for the day, he emerged from the bedroom to find Cassie scrambling some eggs.

“Morning, darlin’” Dean slurred, giving Cassie a kiss on the cheek.

“Sleep well?” Cassie asked, not even looking up from the food she was cooking, but her lips turned up in a soft smile.

The question jump started Dean’s heart into overdrive and he made a noise of surprise, trying to cover it by clearing his throat. His eyes flicked to Cassie’s face. He looked for several seconds to see if there was somehow some kind of knowing look on her face, which was ridiculous because Cassie wasn’t a mind reader.

After a moment, Cassie raised an eyebrow at him in question.

“That good, huh?” She asked, looking a little concerned like Dean might be losing it.

In truth, he might be.

What the fuck was wrong with him?

Maybe the dream was like one of those intrusive thoughts people talked about. You know, like how people have thoughts about driving their car off the road or kissing their sister? He’d had a few before that usually made him deeply uncomfortable and he knew they weren’t truly a reflection of how he felt after doing some very questionable googling. So this must be no different. 

Yeah. It was just an intrusive thought-dream.

Dean brightened a bit, feeling relieved. There was nothing wrong with him. Well, at least not in that way.

He didn’t think too hard about what “that way” meant because he knew it veered into thought territory that would have Sam disappointed in him.

…

Over the next few weeks, Dean continued having these intrusive dreams that got increasingly graphic and came to him nearly every night. It was starting to affect his sleep schedule, but he wouldn’t let that stop him from hanging out with Cas. He really liked the guy’s company. And he could tell Cas wasn’t the best at making friends.

It had been a little awkward the first day or two when Dean laid eyes on Cas as he opened his door and Dean’s mind immediately supplied him with memories of those chapped lips wrapped around his very hard cock, but he was able to snap out of it fairly quickly. And if he had to think about Sam’s stinky socks to get rid of the chub in his pants, who had to know?

Somewhere along the way, Cas let it slip to Dean that he had never seen Die Hard and Dean just could not let that slide. Which is why he took it upon himself to start educating Cas on The Classics as Dean referred to them. Dean made a list in his notes app, adding the titles of movies as he thought of them. When he felt like he had a comprehensive list, he reorganized them into the order in which Cas needed to be introduced to them. Top of the list was the Back to the Future trilogy. 

In turn, Cas decided that Dean needed to be given a cinematic education of his own. Most of the movies he suggested were ones Dean had never heard of and most certainly never would have thought to watch on his own, but the two Dean had seen so far were decent. They were both gay films and Dean started to wonder if that’s all Cas ever watched, but he only put up moderate resistance because Cas was a man who liked men and it would be offensive to show outright disgust at the idea of watching a gay movie. Plus, Dean was kind of curious to see them.

One weekend, Cassie was using their apartment for a girl’s night with her friends because it was her turn to host. All the better for Dean who suggested they hole up in Cas’ apartment (as they always did) and watch one of Dean’s favorites: Tombstone. Cas did not have a couch despite Dean’s constant nagging about how important it was to have a comfortable place to watch movies. Okay, that’s not exactly true. Cas did have a couch, but it was tiny and provided very little comfort, so Dean refused to acknowledge its existence as a couch. Which is why Dean and Cas were sitting on Cas’ queen size bed with a decently sized tv placed on the cheap plywood dresser. Cas apparently got the tv in the breakup like everything else. Dean thanked Cas’ shitty ex boyfriend for that at least.

Dean and Cas sat a respectable distance away with Dean closest to the wall, lying back against the bed frame and hugging a pillow to his chest. 

Out of the corner of his eye, Cas noticed Dean mouthing along to the dialogue. He found it quite cute, though he would not say that to Dean. Not because he was embarrassed to have thought it, but because Dean would get all flustered and the tips of his ears would turn pink. Something Cas found even more adorable, truth be told. But Dean had given Cas a lecture about how guys don’t compliment each other like that. Cas, being a gay man, knew this not to be true, but he knew Dean’s masculinity was fragile. There was something else going on besides the words Dean said which told Cas one thing, but did not match his actions. Dean was touching Cas constantly and spent almost as much time looking at his lips as he did staring into his eyes. Closeted? Maybe. In denial? Most definitely. But everyone was on their own journey of self discovery and Cas wouldn’t push. Unless he found good reason to.

When the credits rolled, Dean announced his intentions to swap out the DVD for another one and make some more extra buttery popcorn. Which was all fine, well, and good. Except for the fact that the only exit from the bed was currently blocked by Castiel’s body. Dean could ask Cas to move, but then he would have to explain why he could not just quickly climb over Cas. It might not be too weird. Cas probably wouldn’t even question it. He tended to just accept Dean and his eccentricities (hangups) with very little concern. But Dean would feel the need to explain… The need to explain that if Dean got that close to Cas, even just for a moment, something very bad might happen. Something Dean didn’t want to happen. Something he desperately wanted to happen. Something that he most definitely was not thinking about so why was it tripping him up so much?

“Dean?” Came the hesitant smoky voice of his friend.

Dean realized he had been paused with indecision for a noticeable amount of time. This spurred him into movement, throwing a leg over Cas’ and aiming for his leg to go over the side of the bed so he could plant a foot on the soft tan carpeting of the floor and quickly make his escape to the kitchen. That was the plan, at least.

Something something best laid plans and all that…

What actually happened was Dean slung his leg over so quickly that he lost his balance, causing Cas to immediately react by grabbing Dean’s hips to steady him. That would be okay, except for the fact that it left Dean basically straddling Cas’ lap. Cas’ big hands were firm as they pressed into Dean’s hip bones through his jeans. Cas was surprisingly strong for a weird nerdy little guy. He did an excellent job of keeping Dean from falling onto his face. 

Dean kind of wished Cas had let him fall on his face. Dean was sort of glad he didn’t.

A beat of silence passed while Dean was just… sitting in Cas’ lap and Cas was just… letting him. Their faces were inches apart, matching shocked expressions tinted with some other emotion Dean would not pick apart right now. 

Dean shifted nervously. Cas’ hands tightened on Dean’s hips, effectively stilling him once again.

Dean wondered why Cas was gripping so tight. Cas sucked in a breath. Dean noticed the faintest dusting of pink high on Cas’ cheeks.

Oh.

Dean once again took stock of his position, hands and feet tingling with a need for something. He was sitting in Cas’ lap. Cas’ hands were still very much on his hips. Cas’ thickening erection was pressed into Dean’s thigh.

Oh, fuck.

Dean’s heart rate skyrocketed at the realization. He should get up. He should quickly exit stage left pursued by bear to give Cas a chance to calm down so they could both pretend this never happened.

Dean could not move.

Like he literally couldn’t move.

Not only because his body would not listen to his brain screaming at him to get up, but because Cas’ strong hands were still holding him in place.

“Dean,” Cas forced the name out. There was something in Cas’ tone that Dean did not like. Like Cas was gearing up to let him down easy. Or worse, ask him to talk about it.

Dean did the only thing he could think of to avoid either of those uncomfortable scenarios, the only thing he knew consistently worked to get him out of a scrape. He surged forward and pressed his lips to Cas’. 

Cas let out a soft, surprised noise, pulling back after a moment to look in Dean’s eyes. Cas was checking to make sure this was okay with Dean.

Dean did not want to think about how okay this was with Dean.

His eyes trailed down Cas’ face to catch on his lips. Before Dean even knew he was doing it, he was kissing Cas again. Quite enthusiastically. Cas gave as good as he got, sliding his hand to the nape of Dean’s neck, grabbing onto him firmly in a way that gave just the barest hint of possessiveness. Dean shivered at the half formed thought. His mind was a little fuzzy right now. Cas pulled Dean in like it was all that mattered in the world right now.

Cas’ tongue was in Dean’s mouth. Searching. Touching. Appreciating. His tongue slid against Dean’s in a way that had them both groaning, breathing heavy. His hips rolled forward and he realized that while Cas was still clearly aroused- more so now- so was Dean. 

It was this thought that pulled Dean out of the endorphin-induced, lavender haze that had momentarily overtaken him. He started to panic.

“Dean…” Cas gripped Dean’s left shoulder, not holding him in place, but attempting to soothe, to comfort.

“This can’t happen.” That was all Dean said before he was out of Cas’ lap and halfway across the room.

Cas trailed after him, calling for him to wait, calling for them to talk about this as he made his way through the apartment. That’s the last fucking thing Dean wanted.

This couldn’t be happening.

“Leave me alone, Cas,” Dean said and it was wholly unconvincing. He did not look back for fear that what he would see would cause him to take pause. He pulled open the door and slammed it behind him. 

Dean thought the slam would be cathartic, but all it did was make him flinch.

He was a coward. He was an idiot. How could he do this? How could he do something like this with a man? His friend? How could he do this to Cassie?

Oh, fuck… Cassie.

Dean looked at their shared apartment door. There was a red white and blue wreath hanging on it that Dean thought was tacky, but bought anyway because Cassie wanted it. Briefly he debated walking over to the door. He considered going in. But he knew what was waiting. Cassie’s friends were probably still in there getting drunk and complaining about their lives. Dean couldn’t get past all of them without someone noticing the state he was in. Even if he could, he would never make it past Cassie's discerning gaze.

He walked past the door. Maybe there was a bar he could go shoot some pool in, get drunk enough to forget what just happened until Cassie’s friends cleared out. Maybe Dean wouldn’t go home at all tonight. Maybe that was for the best.

Chapter Text

Dean Winchester, king of overcompensation, was resistant at first. Freshly 19 and still under his father’s thumb, Dean held a preconceived notion about what it meant to be a “real man” as John Winchester liked to call the set rules about the behaviors that were acceptable for his son.

Real men held the door for a lady. Real men didn’t look at other men. Real men liked cars and classic rock and they swore and they drank and they had bad attitudes and got into fights. Real men did not submit to a woman.

Dean did his fair share of fighting in his youth and he could drink just about anybody under the table. He loved cars and classic rock. Where he failed, however, was in submitting to the “inferior” sex. He loved being under a woman’s thumb. It made his whole body tingly and floaty for hours. 

When Dean met Rhonda Hurley, he was all too happy to let her boss him around and take control in the bedroom. She would tie him up, slap him around a bit, and then make him see stars with that incredible mouth and those talented fingers of hers that Dean saw in his dreams.

When she first broached the topic of fingering him, it was an ordinary afternoon. They were sitting in the Impala, parked at a red light, holding hands like the lovesick kids they were when Rhonda popped the question.

“What would you say to a little backdoor exploration?” She asked, not a hint of self-consciousness at all.

For a second, Dean thought she meant she wanted this exploration to happen on herself. But then Dean saw the devious glint in her eyes and he just knew. A hot and cold shiver racked through Dean’s body and his face became very warm. He had never even considered that option. In fact, it wasn’t even an option in his mind.

“Christ, Ronnie…” Dean huffed.

A car behind them honked and Dean realized the light turned green. He stepped on the gas pedal a little too hard.

“C’mon, Dean,” Rhonda implored, her voice going low and thick. “You can’t tell me you’ve never thought about it.” She inched closer to Dean on the seat and her hand snaked onto his thigh, petting gently, distractingly.

“As a matter of fact, I haven’t .” Dean’s voice in comparison was getting higher, tinged with anxiety. Despite himself, he felt his dick twitch. Whether at the proximity of Rhonda’s hand or the image of Rhonda between Dean’s spread legs or a combination of the two, Dean couldn’t (or wouldn’t) say.

Rhonda chuckled warmly. She could tell what effect she was having on her boyfriend.

“How about we just try it once? And if you hate it, we’ll stop and I’ll never bring it up again. I promise.” She emphasized that promise by squeezing Dean’s thickening erection and nipping at a spot just under Dean’s jaw.

That was how Dean found himself on all fours, ass in the air with three fingers rubbing deliciously at his prostate that very night. Let it not be said that Rhonda Hurley waited to pounce on an opportunity.

“R- ronnie… c’mon… right there. Fuck.” Dean whimpered and begged and gripped the sheets and just overall had an amazing time. 10/10 would try again.

From there they graduated to small toys and plugs that Dean of course resisted (more for appearance’s sake than anything else) and then loved every minute of. He was especially fond of this one sparkly blue vibrator that Rhonda swears she didn’t buy just for Dean so it wouldn’t be “Dean’s Vibrator” because Dean Winchester did not own any sex toys that were meant to be used on chicks or gay guys (not that Dean judged, he was just neither of those things).

By the time Rhonda finally suggested a strap-on, Dean was already pretty warmed to the idea (read: very turned on by it), so there was hardly any protestations left for him to give. He knew he liked having things in his ass and he knew he liked Rhonda being the one to do it. 

The first time Dean took a strap, his mind blanked out. He was blissfully satiated in a way he had never before experienced. Having a body over his, making him feel small and cared for while simultaneously feeling so full was a high unlike any other. It didn’t matter the position, although he did prefer it doggy-style. He took it like a begging, desperate champ and he enjoyed every sweaty second of it. 

When Rhonda moved to California to pursue her dreams and Dean stayed heartbroken in Kansas, he really thought that chapter of his life was over. It was several years and several flings later that he met Cassie and though it took Dean months and a lot of booze, he finally divulged his proclivities and was so relieved when Cassie not only accepted it, but was excited to participate. She never once looked at him differently because of it. It was one of the reasons Dean loved her so much.

…

Two weeks passed without Dean and Cas seeing each other. Cassie never asked why Dean didn’t come home the night she had her friends over. She probably just assumed he fell asleep on Cas’ couch and Dean was not about to correct her. 

In all honesty, Dean just planned to avoid Cas and pretend the whole ‘incident’ never happened. That was working perfectly well for him right up until one afternoon when he was coming home from work and didn’t look where he was going because he was texting Cassie about what to cook for dinner.

Dean walked right into another person, basically smacking his skull against theirs.

“Ow, fuck.” Dean cried, rubbing at the spot where there would probably be a bump later. He looked up to see who he had crashed into and of course it was Castiel.

They both stood there for a moment in shock, eyes locked on one another.

Cas finally broke the tension with a “Hello, Dean,” causing a shiver to go down Dean’s spine.

Dean felt his heart rate pick up. Though whether it was from anxiety or something far more hopeful, he wouldn’t say.

“Hey, buddy…” Dean sighed. “Listen…”

“If you’re going to give me some bullshit speech about how you’re totally straight and what happened last week was just some sort of freak bodily reaction, then you can spare me. I do not need nor want to hear it.” Castiel looked tired. The dark circles under his eyes were more pronounced than ever and there was a weariness carried in the set of his broad shoulders.

“I am straight,” Dean argued, but it sounded unconvincing, even to him.

“Yes, Dean. I’m sure you are… Because straight guys get hard from sitting in the laps of their male friends and straight guys constantly look at the lips of their male friends and then lick their own lips and straight guys love doing it doggy-style with their girlfriend being the one to pound their tight little ass into the mattress while they beg for her hot throbbing cock.”

Dean was stunned into silence. He had never heard Cas say so many dirty things at once. At all, actually.

“How did you- Did Cassie- How would you even know that?” Dean asked in horror.

“I didn’t actually…” Cas laughed, half-surprised half-bitter. “But I do now. Honestly, Dean, nobody cares if you like men. Cassie doesn’t care. But I’m sure she’d care if she knew you kissed somebody else.”

“Are you threatening me?”

“No, Dean. I’m not.” Cas sighed. He appeared to be at war with himself about what to say next. “Look… I like you, Dean.”

Dean’s heart picked up at those words.

“As a friend, of course.” Cas added as an afterthought.

Oh. Something scalding and sharp wriggled in Dean’s stomach.

“Can we just… pretend like nothing happened?” There was a weary sort of desperation that showed in Cas’ whole frame. 

Christ, it was only just now hitting Dean that his hot and cold behavior could be affecting Cas too. Dean was such a self-obsessed asshole. 

Letting the full weight of Cas’ puppy dog eyes affect him, he caved. “Of course, Cas. I’m sorry I’ve been MIA lately. You don’t deserve that shit.”

Cas sighed in relief and his shoulders released a bit of tension.

“Thank you, Dean.”

Castiel’s smile definitely had no effect on Dean whatsoever. No sir. Not one bit.

Motherfucker, Dean was so screwed.

Chapter Text

[Dean and Cas hang out and the tension amps up but Cas refuses to do anything because he doesn’t want to betray Cassie like that. Dean hangs out with Cas, gets amped up, then goes home and get Cassie to peg him]

Dean slammed the apartment door behind him and took a deep breath, looking around the apartment for his girlfriend. He found her when he heard the shower running and her soft voice singing some song Dean couldn’t place.

[Dean gets in the shower and Cassie shoves him into the wall and fingers him while he thinks about Cas]

…

[Dean hangs out with cas and falls asleep at his place. Cas wakes him up because he’s having a nightmare and they end of kissing and then having sex]

…

“I’d just like you to be honest with yourself. For once in your life.”

“Fuck you.”

“Okay, Dean. I’m going to go now. Goodbye.” Cas looked at Dean with pity. Dean hated that look.

“Wait. Maybe I…” Dean looked around as if someone might walk up on them or overhear. “Maybe I do… you know. I don’t know if I do, but maybe. I’m confused, man. I need you. I need your help.”

“I’m not here to be your little experiment while you cheat on your girlfriend, Dean.”

“I’m not asking you to. Just… I just… Please.”

…

[Dean and Cas sneak around, at one point Cassie asks if anything is going on, Dean gets offended, it becomes a fight. Eventually Cassie walks in on them. “You told me nothing was going on an I believed you because we promised each other no more secrets”]

Cas spent the entire last week in a foul mood. He had barely slept the entire week, just trying to figure out what exactly to do about Dean or if he should do anything at all. Logically, he knew what the right thing to do would be: send Dean back to his loving girlfriend and hope he would find some other poor sap to experiment with. But Cas knew he wouldn’t do that. He unfortunately really liked the guy despite his best efforts not to. If he were stronger… though it doesn’t really help anything to obsess over “what-ifs.” Cas is a weak man. At least he is for Dean Winchester. 

From the moment they bumped into each other, Cas had been intrigued, even through his embarrassment at the circumstances in which they met.

…

“Am I not enough for you, Dean? Was it something I did?”

“Fuck, no, Cassie. That’s what makes this so hard. You’re perfect. You’re beautiful and sexy and kind and I love you so much, but when I’m with Cas… I just.. I feel… I don’t know. I feel right. I thought I felt right with you because I love you so much and you’re everything I could ever ask for in a girlfriend.”

“You love me so much but you aren’t in love with me, are you? I’m everything you could ever ask for except I’m not a man. That’s it, isn’t it, Dean?”

“No, I-”

“Dean, don’t lie to me. Lie to yourself all you like, but not to me.”

“You think just because I like to take it up the ass sometimes that I’m gay? How fucking narrow minded are you? I’m not gay. Cas is just.. He’s different.”

“Narrow minded? Dean, you have always been attracted to men. I knew very shortly after I met you when you wouldn’t stop checking Benny out at his Christmas party. It never bothered me. I just thought you liked me too.”

“Maybe I’m bisexual.”

“Yeah, maybe. But you know what that makes you, Dean? A cheater.”

“Cassie-”

“No. It’s one thing to let Cas fuck you because you’re gay and repressed and trying to figure yourself out. It hurts like shit still but I’d understand. But if you aren’t attracted to women- to me- then that’s not a choice you can make. But if you are bisexual and you are attracted to the woman you made a commitment to, then you chose someone else over me. If you’re bisexual, it’s no different than if you had cheated with another woman.”

“It is different, Cass. I was confused and scared and it was driving me crazy not knowing for sure. I had to know for sure.”

“How many times, Dean?” It was a question but it was spat out like an accusation. “Exactly how many times did he stick his dick in you before you ‘knew for sure’?”

“...”

“That’s what I thought.”